Carbon Tetrachloride → 6-Bromomethyl-2-cyclohexyl-benzothiazole

HRID 911327ノート

反応式

HRID 911327 の反応式
[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Br:25][CH2:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([CH:1]3[CH2:2][CH2:7][CH2:6][CH2:5][CH2:4]3)[S:9][C:10]=2[CH:16]=1

参加物

6

反応物 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 508498892-Benzyl-6-methyl-benzothiazole

生成物 1

HCID 576564066-Bromomethyl-2-cyclohexyl-benzothiazole収率 53.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Combine 2-benzyl-6-methyl-benzothiazole (0.6 g, 2.42 mmol), NBS (0.5 g, 2.54 mmol), AIBN (40 mg, 0.24 mmol), carbon tetrachloride (10 mL) and reflux for 3 h. Cool the reaction mixture to ambient temperature, dilute with chloroform and wash with water. Dry the organic extracts over anhydrous Na2SO4, concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) to obtain the title compound as a white solid (0.4 g, 53%). MS (ES+) m/z: 311 (M+H)+.

後処理

  1. washwash with water
  2. dry with materialDry the organic extracts over anhydrous Na2SO4
  3. concentrationconcentrate in vacuo
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1)

出典と根拠

ORDレコード
ord-bfa01b655c134fa38693c1c683fbef7f
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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